


Not just tonight, maybe forever

by FabulousMoose



Category: Critical Role (Web Series)
Genre: Established Relationship, Explicit Sexual Content, F/M, Freeform, Light Bondage, M/M, Plot What Plot/Porn Without Plot, Threesome - F/M/M
Language: English
Status: Completed
Published: 2020-12-27
Updated: 2020-12-27
Packaged: 2021-03-11 09:22:45
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,964
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28349103
Author URL: https://archiveofourown.org/users/FabulousMoose/pseuds/FabulousMoose
Summary: Caleb takes his belt and looks at Essek."I want to tie you up? Is that okay?""Last time you tried to cuff me, you were going to put me on a Sleep spell," Essek's smile is everything but friendly. But Caleb knows it's just a mask he tries to put on to hide how vulnerable he actually feels."Last time, I wasn't trying to make you come," Essek takes a deep breath. "You can say no. It's alright," Essek stays silent for a few seconds. Jester pats his shoulder in a comforting way. Caleb smiles at her softly before looking at Essek again.
Relationships: Essek Thelyss/Caleb Widogast, Jester Lavorre/Caleb Widogast, Jester Lavorre/Essek Thelyss
Comments: 4
Kudos: 47





	Not just tonight, maybe forever

They had arrived at the Kryn outpost in the late afternoon. They were exhausted and almost without any spells left. Essek and some of the Kryn guards were already waiting for them outside.

Jester, who was walking beside him, let go of his hand to run towards Essek. Caleb saw some of the guards slightly tense their weapons but a hand gesture from the Shadowhand was enough for them to regain their composure.

He looked as he always did. Elegant, proud, and surrounded by an energy that gave off an exciting and dangerous aura.

The stoic and stern visage of Essek Thelyss breaks for a second into a slight smile when Jester hugs him. She whispers something to him, and Caleb sees him shake his head, still with a smile on his face.

"Welcome, Mighty Nein." Essek salutes as the rest of the party catch up. They're not as affectionate as Jester. Caduceus pats Essek on the shoulder, and Yasha waves awkwardly. The rest still feel a bit wary and hurt, but they know they'll need Essek's help. " It's good to see you all safe. " Essek adds, looking at Caleb directly. Caleb gives a slight nod but doesn't say anything.

Jester threads her arm through Essek's as they start walking, the rest of the party following behind. She starts telling him about Traveler Con and all the shenanigans that happened on the island.

They are led to a small chamber where dinner is apparently ready and served. They eat and do some unimportant small talk before they are taken to their respective rooms. They had decided that they could talk about important business the next day in the tower, away from prying eyes and ears.

Jester intertwines her fingers with Caleb's as they enter Caleb's room.

Caleb had just taken off his holsters when someone knocks at the door.Jester, who had just taken off her coat and boots, walks towards the door and opens it.

She meets a surprised Essek holding a bottle of wine.

"Jester, " he says, with an unusual tone of voice. Essek gives Caleb a glance. " I'm sorry to interrupt. I didn't know you were here.I thought Caleb was alone, " There's a slight flush in his face, and Caleb can't help but feel intrigued because Essek coming to his room was the last thing he had expected. Jester looks over her shoulder and meets his gaze. Her eyes asking what he wants to do. Caleb shrugs.

"Is there something you wanted, Shadowhand?" he asks, taking a few steps forward. It's the first time since arriving that he talks.Essek takes a deep breath and meets his eyes. He opens his mouth before reconsidering it and shakes his head.

He smiles at them, but it doesn't reach his eyes.

"Nothing that can't wait until tomorrow. I apologize again for interrupting your night. You're probably very exhausted after such a long journey."

"No, Essek!" Jester says, reaching out and grabbing him by the arm. Essek stops."You clearly wanted to talk about something with Caleb. I can leave for a few minutes if you want. It's not a problem, " Jester smiles at him.

Essek looks a little torn before he shakes his head again.

"It's alright, Jester. It can wait. " He gives her the bottle of wine. " I... I didn't know you two were an item. I'm glad for you." Essek looks at Caleb and nods. " Good night."

Essek turns around when he feels Jester grab his hand.

"You know, I don't really drink alcohol. But Caleb does, and it feels rude that you would let him drink alone. You brought it with you, after all. " Essek looks confused as Jester lets go of his hand and she enters the room again.

She gives the bottle to Caleb and sits in the bed, expectantly. She winks at him and Caleb feels like his heart is going to explode at the meaning behind her glance.

"You decide, Shadowhand," Caleb says after a few seconds, putting the bottle on the nightstand. "You can either close the door and leave. Or close the door behind you and stay. "Essek feels shocked for a moment, apparently not expecting this outcome. But he recovers quickly.

He takes a few steps forward and closes the door behind him.

Caleb looks at Jester to check if she's still on with this. She smiles at him and gives him an encouraging nod.

She stands up from the bed and continues to undress. Essek watches her in silence as Caleb watches him.

"Beautiful, isn't she?" he whispers in his ear.

Essek shudders, not expecting the closeness, before nodding.

“I want you to stand on your feet,” he orders next. Essek looks up and meets his blue eyes. Two seconds later, Essek stops hovering and his feet touch the floor. “Take off your cloak,” Essek does as Caleb orders and lets the elegant purple mantle fall to the floor. “Now sit at the edge of the bed,”

Essek takes a deep breath before he walks towards the bed. Jester, who's now wearing a white silky nightgown, looks delighted at Essek.

Caleb takes off his satchel and his boots. He rolls up his sleeves. He takes off his ponytail, letting his hair fall on his shoulders before putting it up again so it doesn't stand in the way.

"Jester, " Caleb says, offering her a hand. She intertwines their fingers and Caleb pulls her in before kissing her deep and hot.

He grabs her face, and Jester moans as his tongue explore her mouth. Her tail curls around his thigh, teasing his hardness through the fabric, as she presses herself towards him to find friction.

Caleb groans in her mouth before they pull away to catch their breath.Jester looks at Essek and there's an intense hunger in his eyes.

She winks at him.

"Here are some rules, " Caleb says, as he walks to stand in front of Essek. "I will tell you what you can and can't do" He touches his cheek and Essek's eyes close for a few seconds, enjoying the contact. " If it's too much, you'll tell us. If you have to take a few seconds, you will tell us. If there is something you don't want, you will tell us." Caleb's fingers brush his lips. "That door is closed, but you can always leave when you want to. Do you understand?" Essek nods, feeling the anticipation vibrate on his skin. Caleb grabs his chin, a little tight, forcing him to opens his eyes. " Do you understand?" he asks again, more serious.

"Yes, Caleb," he whispers, swallowing with difficulty.

"Good," Caleb releases his grip and looks at Jester. "Take off his shirt." Jester gives a soft laugh before she sits behind Essek, pressing her chest on his back, and she begins to unbutton his shirt without difficulty.

She nuzzles Essek's neck, giving him small kisses on his skin, and as his hand starts to move towards her, she slaps it and puts it down.

"No touch," she reprimands Essek. Caleb smiles as he watches her undress the drow. "Grab the sheet." Essek groans but does as she says. He looks at Caleb expectantly and Caleb just raises his eyebrows.

Jester takes off the shirt and it falls on the floor. She starts kissing his neck again and Essek's head tilts back to give her more access.

Essek's body reacts delightfully as Jester's hands travel through his body, exploring and teasing. His body arches up with each touch demanding more. Jester sits on his lap and her fingers brush his face softly.

Then she moves her hips slowly, rubbing herself on Essek and both of them moan at the friction. Caleb's cock becomes harder with just the view. His breath hitches and his throat goes dry.

He sees Essek's hands grab the sheet tightly as Jester continues to rock her hips in delicious torture. Caleb stands behind Jester and touches her skin, pulling her nightgown up. She stops moving, almost reluctantly and Essek whines, looking up at Caleb.

Caleb's fingers disappear between her legs. Jester has to grab Essek's shoulders to hold on as Caleb starts to play with her.

She moans aloud as Caleb's wet fingers tease her entrance. She rests her forehead on Essek's and her hips arches for more contact.

Essek whines, feeling like his body is on fire and it's about to explode.

"Do not come until you are told to," Caleb warns him. Essek groans but nods. "Kiss him, Jester," The tiefling grabs Essek's face and kisses him hard.

Essek uses all his will power to not touch Jester. Her tongue explores his mouth with confidence and he moans when she bites his lower lip.

Jester spreads her legs as Caleb's introduce a finger inside her. She whimpers, losing her breath for a moment. She feels hot and the tickling of her belly increases with intensity.

She cries when Caleb suddenly retrieves his fingers.

"Kiss him," he whispers in her ear. She grabs Essek by the hair, making him groan, and kisses him again.

Caleb's fingers return and she moans, satisfied again. Essek's hips thrust up, trying to find some kind of friction, feeling a bit frustrated.

"Please, " he whispers in Jester's mouth, begging with his eyes.

"What do you want, Essek?" Caleb asks, looking over Jester's shoulder as he continues to finger her.

"I want _you_ to touch me," the drow whimpers. Caleb smiles and kisses Jester's neck before he pulls out his fingers from inside her. She cries in protest.

Jester moves from Essek's lap and lies on the bed. She starts touching and pleasuring herself. It's a breathtaking view, but Caleb's focus needs to be on Essek.

"Where do you want me to touch you, Essek Thelyss?" Caleb asks in a hoarse voice.His Zemnian accent even more pronounced.

"Everywhere, " the drow answers, closing his eyes. Jester's moaning in the background is a delicious melody for them.

"Do not touch me," Caleb reminds him. He grabs Essek’s hair and pulls his head back, making him groan. " Like this? " He whispers in Essek's face. Caleb's lips brush his skin, slowly touching his cheek and his forehead, before brushing his swollen lips. Essek grunts and Caleb decides to award him.

He kisses Essek slowly and carefully like he is something delicate. As the kiss progress, the kiss becomes deeper and more demanding.

Without breaking the kiss, Caleb starts to undo his pants, until they are loose and he throws them aside. His cock comes free, grateful for the sweet release.

He sits on Essek's lap and carefully straddles him, making friction with his cock through the fabric. Essek groans in his mouth, arching up, making him move a little bit faster.

From the corner of his eye, he sees Jester approaching. Her skin has a slight purple color and her forehead is covered in sweat. She has taken off the rest of her clothes and now is completely naked. She smiles at him before she nibbles Essek's lobule, making him shudder.

Caleb rubs his cock in Essek’s warm skin and Essek's body starts to shake.

"I'm going to come," he whispers in his mouth. Caleb kisses him hard before standing up. Essek whimpers but does not protest.

Caleb takes his belt and looks at Essek.

"I want to tie you up? Is that okay?"

"Last time you tried to cuff me, you were going to put me on a Sleep spell," Essek's smile is everything but friendly. But Caleb knows it's just a mask he tries to put on to hide how vulnerable he actually feels.

"Last time, I wasn't trying to make you come," Essek takes a deep breath. "You can say no. It's alright," Essek stays silent for a few seconds. Jester pats his shoulder in a comforting way. Caleb smiles at her softly before looking at Essek again.

"Not too tight, " he finally accepts. Caleb nods and gives him a slow kiss. Essek lets him take control again, and the tempo has returned to the room. 

"Get on the bed and lie on your back," Caleb orders him. "Put your hands over your head,"Essek does as he is told. Jester giggles as she takes the belt and ties up Essek's hands.

Caleb kisses her deeply over Essek's body. Jester grabs Caleb by the hair, deepening the kiss and Essek feels his mouth dry up as he watches them kiss like there's no enough air in the world.

Caleb's mouth runs through her skin, leaving traces of kisses behind. His mouth captures her nipple and he bites it, making her moan. He plays with her breasts for a moment before his mouth wanders down. Both Jester and Essek stay still and they look expectantly as Caleb moves closer to her cunt, but he stops and looks at Essek instead, with a smug grin on his face.

"How about we see how that mouth of his works, instead?" He asks Jester. Jester nods. " How about you, Thelyss? Do you want Jester to fuck your pretty face?" Essek grunts, unable to use his words, and nods.

Caleb helps Jester position herself comfortably, Essek's face between her legs. Caleb kisses her one last time and she lets out a loud moan when she feels Essek's mouth on her.

He traces his fingers in Essek’s skin until he reaches the waistband of his pants. He pulls them down until he takes them off. Essek's cock raises almost immediately, hard and swollen.

Caleb reaches one of his special oils and pours a large amount into his hand.With that, he wraps his hand around Essek's cock and begins to stroke him slowly. He hears Essek's moans, hidden under Jester's legs.

He puts some pressure as he focuses on the head with his other hand, making some circles with his fingers. He increases the speed, putting him on edge. Essek's body trembles as his hips thrust up, his face still between Jester's thighs.

Caleb slows the speed again and Essek whimpers.

He increases the speed, stroking him harder before he swallows him whole. Caleb moans as he savors the salty taste of Essek’s pre-cum. He licks and kisses his length, slowing down the pressure.

"Please, " Essek whimpers under Jester. Caleb smiles and stops touching him.

Essek whines and Jester grabs his hair and redirects his face towards her clit. Essek hungrily complies. Jester moves her hips frantically as Essek sucks her clit, making her whole body start to tremble.

Seeing as Jester is soon reaching her climax, Caleb spreads Essek’s legs and sits between them before he starts to jerk him off. He rubs his cock with Essek's and starts to stroke them together. Essek moans and keeps driving Jester towards the edge.

Jester's body shakes, reaching her climax. Essek licks her fluids before Jester moves and lies beside him, exhausted and satisfied. She gives him a shy smile before kissing him, tasting herself on his lips.

Caleb increases his grips and starts to feel himself lose control.

"Come for me, Essek, " He orders. The drow moans, thrusting himself up a few more times before he spills his seed between Caleb's fingers. Caleb comes not long after that, spilling himself on Essek’s stomach and chest.

For several minutes only their shaky breaths are heard.

He stands up and unties Essek's hands before getting a wet towel to clean them.

"I could have helped with that" Essek says, breaking the silence. Caleb looks up and smiles.His hair, normally well combed, is totally disheveled.

"But there is no fun in that, " he responds taking his hand and giving it a soft kiss,where the belt had slightly tightened his skin.

"Andthen there is no intimacy of taking care of each other afterward, " Jester adds fixing his hair, fondly.Essek looks down for a moment before he nods.

Jester kisses him on the shoulder before she stands up and puts on her nightgown. Caleb puts on the pants he normally sleeps in.

Essek clears his throat as he stands and looks a bit awkward.

"I should probably go to my chambers before someone thinks I've disappeared, " he starts saying, without meeting their eyes.

"Or you could spend the night if you want," Jester says, hopeful.

"You're welcome to stay here if you want, Essek. " Caleb adds taking his hand. He intertwines their fingers.

"Your friends might wonder what I'm doing here," he says with a sad smile.

"They can think what they want,"

"My people might wonder what I'm doing with imperial people, "

"We're not holding you hostage and you can leave, but we want you here, Essek,”

"Just tonight, though?" Essek asks in a small voice. Caleb grabs his face softly and forces him to meet his eyes.

"Too much has happened and there are still some open wounds, but we want you with us as long as you want us with you. Not just tonight, " Caleb kisses him sweet and short before releasing him. He walks towards Jester and kisses her head.

There's a little voice in Essek's head that says that this is a bad idea and he shouldn't, that he doesn't deserve it. But he is tired of being alone, of feeling alone and empty every night and these two beautiful and wonderful people want him and they like him enough to share their precious space with him.

He picks up his mantle and puts it on the chair before walking towards them.

Jester smiles and throws herself into his arms before she kisses him. Caleb kisses him on the temple.

They go to bed with Essek sleeping in the middle, Jester wrapping herself around him like an octopus, and Caleb resting his head on his chest.

He sleeps better than he has in decades.

**Author's Note:**

> First time writing about the ship between Caleb+Essek+ Jester. I'm testing the waters, so sorry for anything that you didn't like or was weird. And I also apologize for any gramatical error! 
> 
> I had an itch and I had to write something to survive without Critical Role. Anyway happy Hollidays! May 2021 be kinder <3


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